1',2,3,3',4,4',6-hepta-O-acetyl-6'-O-TBDMS-sucrose | 63734-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1',2,3,3',4,4',6-hepta-O-acetyl-6'-O-TBDMS-sucrose
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2-(acetyloxymethyl)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 63734-14-5
• 化学式: C₃₂H₅₀O₁₈Si
• 分子量: 750.824
• InChiKey: ZGBCGKHPHOWGAS-MICPXKNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  51
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1',2,3,3',4,4',6-hepta-O-acetyl-6'-O-TBDMS-sucrose 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 0.5h， 以82%的产率得到1',2,3,3',4,4',6-hepta-O-acetyl-6'-O-formyl-sucrose
  参考文献：
  名称：

  Facile conversion of O-silyl protected sugars into their corresponding formates using POCl3·DMF complex

  摘要：

  The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex (POCl3DMF)-D-. was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.056
• 作为产物：
  描述：

  乙酸酐 、 叔丁基二甲基氯硅烷 、 蔗糖 以 吡啶 为溶剂， 以35%的产率得到1',6,6'-tri-O-TBDMS-2,3,3',4,4'-penta-O-acetyl-sucrose
  参考文献：
  名称：

  Facile conversion of O-silyl protected sugars into their corresponding formates using POCl3·DMF complex

  摘要：

  The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex (POCl3DMF)-D-. was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.056